South Windsor Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for South Windsor holiday rentals

Smart TV
Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
2.0 star property
South Windsor
The price is HK$429
HK$649 total
includes taxes & fees
1 Jan - 2 Jan 2026
Entire guest suite in South Windsor, Connecticut
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (34)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is HK$926
HK$2,176 total
includes taxes & fees
27 Dec - 28 Dec
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Property grounds
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (12)
"Very nice country stay. "
United States
michael C.
The price is HK$1,470
HK$2,748 total
includes taxes & fees
1 Jan - 2 Jan 2026
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Terrace/patio
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (30)
"Great host- fun property!"
United States
Mary F.
The price is HK$910
HK$2,328 total
includes taxes & fees
6 Jan - 7 Jan 2026
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Interior
Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (5)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is HK$926
HK$2,122 total
includes taxes & fees
20 Jan - 21 Jan 2026
Modern & Cozy Cape | 4 Bedroom House | Central Location
Beach nearby, beach towels
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
The price is HK$933
HK$2,185 total
includes taxes & fees
28 Dec - 29 Dec
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (48)
"Very nice place to get away and enjoy the lake! Host responded very quickly and was very helpful! Would book again. "
United States
Rachel G.
The price is HK$995
HK$2,249 total
includes taxes & fees
5 Jan - 6 Jan 2026
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds
Humble Abode #2

Humble Abode #2

Humble Abode #2
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (1)
"the place was clean bed was nice"
United States
Jonathan
The price is HK$933
HK$1,229 total
includes taxes & fees
1 Jan - 2 Jan 2026
Humble Abode #2
Exterior
Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (29)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
United States
Jennifer H.
The price is HK$918
HK$2,168 total
includes taxes & fees
7 Jan - 8 Jan 2026
Treehouse - Countryside - Farm Animals - Fire Pit
Exterior
The Blue Back Bungalow

The Blue Back Bungalow

The Blue Back Bungalow
2.0 star property
West Hartford
9.4 out of 10, Exceptional, (18)
"The stay was good. The house is located in a great area and very close to my family member we were visiting. I will stay again and make sure everything is in order. "
United States
Vanessia P.
The price is HK$622
HK$2,427 total
includes taxes & fees
30 Dec - 31 Dec
The Blue Back Bungalow
Interior
Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home

Cozy Guest Suite in Historic Home
Middletown
10.0 out of 10, Exceptional, (1)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is HK$1,148
HK$1,670 total
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Guest Suite in Historic Home
Interior
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
2.0 star property
Manchester Center
10.0 out of 10, Exceptional, (5)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is HK$933
HK$1,557 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Smart TV, computer monitors
Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is HK$671
HK$1,635 total
includes taxes & fees
5 Jan - 6 Jan 2026
Central Chic Pad - with Free Parking, Heat & AC
Exterior
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (25)
"Hosted a bachelorette trip at this property and it was fantastic. The kayaks and paddle boards provided plenty to do along with a firepit to sit around at night. The house was cozy with plenty of space to sleep 5. Had a great time! "
United States
Renee J.
The price is HK$1,244
HK$2,590 total
includes taxes & fees
29 Dec - 30 Dec
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Smart TV
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Manchester
9.4 out of 10, Exceptional, (14)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is HK$848
HK$2,079 total
includes taxes & fees
5 Jan - 6 Jan 2026
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Terrace/patio
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin
Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is HK$966
HK$2,509 total
includes taxes & fees
5 Jan - 6 Jan 2026
Soothing 2-bedroom lower-level apartment in Berlin
Outdoor dining
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.4 out of 10, Exceptional, (20)
"We had a nice getaway after a tour of our alma mater, UCONN. This welcoming and very well decorated home gave us a nice place to rest and connect after our busy day."
United States
Andrea F.
The price is HK$1,097
HK$2,397 total
includes taxes & fees
8 Jan - 9 Jan 2026
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior
Family Stays: Middletown, CT

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (19)
"The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!"
United States
Cari M.
The price is HK$972
HK$1,841 total
includes taxes & fees
6 Jan - 7 Jan 2026
Family Stays: Middletown, CT
Property grounds
Welcome to Honey Spot!

Welcome to Honey Spot!

Welcome to Honey Spot!
Pine Point
9.8 out of 10, Exceptional, (27)
"Ricardo was a great!!made are stay wonderful was very helpful and went out of his way to make or stay great we had a good time place was beautiful something for everyone will definitely stay here again thank u"
United States
Marie A.
The price is HK$1,011
HK$2,294 total
includes taxes & fees
31 Dec - 1 Jan 2026
Welcome to Honey Spot!
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford
Downtown Hartford
8.6 out of 10, Excellent, (24)
"Great stay"
United States
Josh H.
The price is HK$778
HK$1,184 total
includes taxes & fees
26 Dec - 27 Dec
Lux Boutique Large Private LOFT Pratt St Hartford
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Windsor Hotel Reviews

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"Clean room and Bed. BUT the TV definitely needs a upgrade. Very small and outdated "
Jeffrey 1-night trip
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Springfield MA

Find out more about South Windsor

Search for holiday rentals in South Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in South Windsor using one of the methods below:

  • View our selection of featured holiday rentals in South Windsor
  • Use the map to find apartments and other holiday homes in the South Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Windsor while they last

Look no further and take a look at our great range of rental properties in South Windsor!

Frequently asked questions

Are there holiday rentals in South Windsor?

Yes, there are holiday rentals in South Windsor close to Nomads Adventure Quest, or you can select a more secluded option if you're looking for a relaxing stay. South Windsor is known for its shopping and golf courses. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best holiday rentals that South Windsor has to offer?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: This holiday home rental outside of South Windsor offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in South Windsor?

Connecticut River and South Windsor Bark Park are a couple of scenic spots to enjoy the outdoors, whereas Wood Memorial Library & Museum is one of the cultural attractions. Other places in town to visit include Nomads Adventure Quest and Promenade Shops at Evergreen Walk.

What’s a holiday rental in South Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Windsor. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.